Croatica Chemica Acta, Vol. 64 No. 4, 1991.
Original scientific paper
Stereochemical Studies of some 12a-Substituted Rotenoid Derivatives
Ivanka Kostova
; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Nikolina Berova
; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Petko Ivanov
; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Bozhana Mikhova
; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Rositza Rakovska
; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Gunther Snatzke
; Lehrstuhl fur Strukturchemie, Ruhruniversitat, Postfach 10 21 48, D-4630 Bochum, Germany
Abstract
The absolute configuration at 6a and 12a positions as well as the conformation of rings B and C of some cis fused 12a-substituted (OH, CH2OH, CH2OCOR’) synthetic derivatives of natural rotenoids, rotenone and amor- phigenin, are discussed on the basis of 'H NMR, CD and molecular mechanics studies.
The CD Cotton effects above 300 nm of all 12a-substituted derivatives, compared with those of the parent natural rotenoids, show an unexpected sign inversion and cannot be used for reliable configurational assignment. This has been achieved in a nonempirical way by application of the exdton chirality method.
Keywords
Hrčak ID:
137272
URI
Publication date:
29.2.1992.
Visits: 1.027 *